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Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenes to Cyclobutenes.


ABSTRACT: A highly efficient palladium-catalyzed oxidative borylation of enallenes was developed for the selective formation of cyclobutene derivatives and fully-substituted alkenylboron compounds. Cyclobutenes are formed as the exclusive products in MeOH in the presence of H2 O and Et3 N, whereas the use of AcOH leads to alkenylboron compounds. Both reactions showed a broad substrate scope and good tolerance for various functional groups, including carboxylic acid ester, free hydroxy, imide, and alkyl groups. Furthermore, transformations of the borylated products were conducted to show their potential applications.

SUBMITTER: Qiu Y 

PROVIDER: S-EPMC5021125 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenes to Cyclobutenes.

Qiu Youai Y   Yang Bin B   Zhu Can C   Bäckvall Jan-E JE  

Angewandte Chemie (International ed. in English) 20160418 22


A highly efficient palladium-catalyzed oxidative borylation of enallenes was developed for the selective formation of cyclobutene derivatives and fully-substituted alkenylboron compounds. Cyclobutenes are formed as the exclusive products in MeOH in the presence of H2 O and Et3 N, whereas the use of AcOH leads to alkenylboron compounds. Both reactions showed a broad substrate scope and good tolerance for various functional groups, including carboxylic acid ester, free hydroxy, imide, and alkyl gr  ...[more]

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